Triethylamine → HCID 71008795, compound

HRID 1887503Notes

Reaction equation

HRID 1887503 reaction equation
Cl.[NH2:2][CH:3]1[CH2:22][CH:6]2[C:7](=[O:21])[N:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)[CH2:9][CH:5]2[CH2:4]1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30](Cl)(=[O:32])=[O:31].CCN(CC)CC>ClCCl>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH:2][CH:3]1[CH2:22][C@@H:6]2[C:7](=[O:21])[N:8]([C:10]3[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=3)[CH2:9][C@@H:5]2[CH2:4]1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 131730792HCID 131730792, compound

Product 1

HCID 71008795HCID 71008795, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one, hydrochloride (60 mg, 0.18 mmol), 2-chlorobenzene-1-sulfonyl chloride (76 mg, 0.36 mmol) and Et3N (82 mg, 0.81 mmol) were added to dichloromethane (2 mL), the mixture was stirred for overnight. The solvent was removed, and the crude product was purified by prep-TLC (petroleum ether/ethyl acetate=1:1) to yield the title compound (30 mg, 33%). 1H NMR (300 MHz, CDCl3): δ 8.14-8.11 (m, 1H), 7.68-7.49 (m, 5H), 7.26-7.22 (m, 2H), 5.04 (d, 1H, J=6.6 Hz), 4.05 (t, 1H, J=9.0 Hz), 3.68-3.62 (m, 2H), 3.08-3.06 (m, 1H), 2.79-2.76 (m, 1H), 2.26-2.19 (m, 2H), 1.95-1.93 (m, 1H), 1.73-1.65 (m, 1H); LC-MS: 475.0 [M+1]+.

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified by prep-TLC (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-787580a4497c40ba8d07e59559dbf287
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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